Abstract

Azulenes and acetylenedicarboxylates react under acid catalysis (Brønsted or Lewis) and form (2aRS,8aSR)-2a,8a-dihydrocyclopenta[cd]azulene-1,2-dicarboxylates as intermediate products, which then dimerize by central bond-formation between C(2a1) and C(2’a1) and various peripheral C,C’-atoms of the dihydroazulene fragments, depending on the substituents present. The reactions are often accompanied by the formation of side-products, such as 2-(azulen-1-yl)fumarates and -maleates and others caused by H-shifts of the primary intermediates. H-Shifts between the two tetrahydrocyclopenta[ cd]azulene parts of the heptacyclic structures were also found.

Abstract

Azulenes and acetylenedicarboxylates react under acid catalysis (Brønsted or Lewis) and form (2aRS,8aSR)-2a,8a-dihydrocyclopenta[cd]azulene-1,2-dicarboxylates as intermediate products, which then dimerize by central bond-formation between C(2a1) and C(2’a1) and various peripheral C,C’-atoms of the dihydroazulene fragments, depending on the substituents present. The reactions are often accompanied by the formation of side-products, such as 2-(azulen-1-yl)fumarates and -maleates and others caused by H-shifts of the primary intermediates. H-Shifts between the two tetrahydrocyclopenta[ cd]azulene parts of the heptacyclic structures were also found.

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